Fall in the Berkshires – 6 Reasons to Visit the Berkshires this Fall!

by Global Viewpoint
Fall in the Berkshires Massachusetts

Why visit the Berkshires in the fall?

Fall is the best time to visit the Berkshires, hands down. From leaf peeping and apple picking to country fairs and rustic farms, this region is among the best places to spend autumn in New England. It’s just a few hours from Boston and NYC, but you wouldn’t know it when you’re standing in this untouched autumn oasis.

As a native Bostonian, I’ve had the chance to explore the Berkshires during different seasons. The fall months are my favorite, by far, because of the reasons above. But why choose the Berkshires over other places in New England? Here are 6 compelling reasons why you should visit the Berkshires this fall!

Looking to book a trip to the Berkshires soon? Check out my curated travel itinerary below!

Fall in the Berkshires pinterest pin photo
Fall in the Berkshires pinterest photo
Berkshires itinerary Curated Planet

1. Unspoiled nature and fun outdoor adventures

Located in scenic Western Massachusetts, the Berkshires is a hiker’s haven and a dilettante’s dream. During the autumn months, the entire region is bursting with intense fall foliage. Mountains and streams are covered by the flair of red and orange leaves – it’s a spectacular sight!

Perhaps one of the best vantage points is Massachusetts’ tallest mountain, Mount Greylock (3,489 ft.). From here, you can overlook 5 states on a clear day.

Additionally, this time of year lends itself to exhilarating outdoor activities including kayaking, canoeing, and zip lining. One of my favorite memories from my recent trip was canoeing down the Housatonic River on a guided tour with Berkshire Canoe Tours. Hilary Bashara, who has owned this family-run tour for 19 years, is exceptionally knowledgeable and passionate about the local environment and community. It was wonderful paddling on a canoe, while learning about the wildlife and soaking in the fall ambiance around me.

Whether you’re an outdoor enthusiast or someone seeking a break from the hustle and bustle of the city, fall in the Berkshires will leave you in awe.

Berkshire Canoe Tours is among the best nature excursions in the Berkshires
Berkshire Canoe Tours is among the top outdoor attractions in the Berkshires.

2. Charming inns

In the Berkshires, you’ll find many warm and welcoming B&Bs that each have their own unique story, vibe, and décor. Among these intriguing guest houses, I was particularly impressed with the Harbour House Inn and Chambery Inn.

Built in 1793, the Harbour House Inn is a historic, colonial-style home that embodies the charm of the Berkshires. Each of its 6 guest rooms offer an enchanting ambiance and all the amenities for a comfortable stay.

Each morning, the innkeeper, Jen Showalter, concocts a hearty gourmet breakfast using delicious local ingredients! One of my fondest memories from the Inn was spending breakfast conversing with fellow guests over interesting current events. Given our busy, hurried lifestyles, I feel that a friendly breakfast setting presents a wonderful opportunity to engage with our peers.

Harbour House Inn is one of the most historic houses in western Massachusetts
Harbour House Inn is a great place to spend during the fall months in the Berkshires.

Another inn that embodies the spirit of fall in the Berkshires is the Chambery Inn. Once a 19th-century schoolhouse, the Chambery Inn is a French-inspired B&B with 9 spacious suites. Each room is equipped with a fireplace and whirlpool tub, perfect for rest and relaxation!

One of my favorite experiences at the Chambery Inn was its homemade breakfast. Every morning, the innkeepers deliver a breakfast basket to each room— the best way to start the day.

Particularly during the stunning autumn months, each of these inns offer a unique lodging experience in the heart of the Berkshires!

Chambery Inn is one of the top hotels in the Berkshires
The Chambery Inn is another local favorite when visiting the Berkshires.

3. Captivating museums

On a rainy fall day in the Berkshires, you won’t have to twiddle your thumbs or risk water damaging your camera. Instead, hop into one of the region’s many museums and learn about the heritage behind this beautiful destination.

For those seeking a dose of art, culture, and history in their next vacation, look no further than the Berkshires! During my visit, I stopped by several museums that each had something special to offer. At the Norman Rockwell Museum, it was fascinating to learn about Norman Rockwell’s magnificent artwork and legacy on American history. From “The Four Freedoms” to “Home for Christmas”, Rockwell’s collection is truly an artistic inspiration.

It was also a pleasure checking out the Massachusetts Museum of Contemporary Arts (Mass MoCA) in North Adams. This factory-turned-art-museum is one of the largest contemporary art galleries in the United States. Much of the visual art on display is edgy and eccentric, which makes for a thought-provoking and unconventional experience.

My favorite museum of all is the Hancock Shaker Village in Pittsfield. Established in 1791, Hancock Shaker Village is a historic landmark and museum that offers a glimpse of the simple and rustic lifestyles of the Shakers. Similar to the Quakers, the Shakers were a Christian sect that passionately practiced pacifism, equality, and sustainability.

Inside this village, you’ll find historic buildings and artifacts, handicraft exhibitions, and farm animals that bring the Shaker community to life. Whether you’re planning a weekend trip or extended getaway to the Berkshires, make sure these museums are on your list!

Hancock Shaker Village is one of the top attractions in the Berkshires
Hancock Shaker Village is one of the top things to see and do in the Berkshires.

4. The Berkshires is praised for its farm-to-table dining.

What better way to experience a new place than through its food? With the autumn harvest in full swing, fall in the Berkshires is a great time to eat your way through its amazing restaurants.

After a long day exploring the fall foliage, it’s nice to stop by local restaurants and diners for a taste of the local cuisine. One thing that the Berkshires does extraordinarily well is farm-to-table dining. Many restaurants and B&Bs integrate locally-sourced ingredients into their menus, which come from the fall harvest. Cider donuts, anyone?

In particular, I was impressed by Trail House Kitchen in North Adams. Named after the nearby Appalachian and Mohawk trails, Trail House Kitchen is a family-run restaurant with a beautiful outdoor patio and delicious comfort food. My favorite dishes were the beef medallions and pomegranate cheesecake, which were truly out of this world!

In addition to trying dishes at local restaurants and cafes, I also made the obligatory stop to Chocolate Springs Café in Lenox. This confectionery shop is a chocolate lover’s dream. I’d even argue that it produces some of the finest chocolate in the world. As a self-proclaimed chocolate connoisseur, I was most impressed by the hot chocolate and passion fruit chocolate bars. After endless sightseeing in the Berkshires, a tasty treat is much needed.

Trail House Kitchen is one of the best restaurants in the Berkshires
Trail House Kitchen is a wonderful local restaurant in the Berkshires.

5. Country fairs and other special events

There’s always something exciting happening in the Berkshires, especially during the fall months.

Locals and visitors alike are drawn to the region for its festivals and fairs. Here are some of the popular ones you can’t miss:

6. Relaxation and inspiration in the Berkshires

Aside from its activities and attractions, the Berkshires fosters a serene atmosphere perfect for relaxation.

As you’re gazing at the fall foliage and dramatic landscapes, it’s easy to disconnect from your otherwise busy lifestyle and live (and feel) in the moment. Feeling the cool, gentle breeze as the vibrant-colored leaves sway in the air. Waking up every morning to the smell of livestock and birds chirping. Taking a deep breath and feeling inspired by the stunning scenery. These are some of the surreal experiences that will draw you to the Berkshires, year after year.

Especially during the fall foliage season, you will feel enlivened by the natural beauty and deep serenity of the Berkshires.

  • Thinking about visiting the Berkshires? Check out Berkshires.org – your quintessential planning guide to ensure a wonderful stay in the Berkshires!
Berkshires in the fall pinterest image
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Read next: The 11 Coolest Vacation Rentals in Massachusetts

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Fall in the Berkshires – 5 Reasons to Visit the Berkshires This Fall! | The Berkshires Official Website October 22, 2018 - 15:45

[…] Just a 3-hour drive from Boston and NYC, the Berkshires of Western Massachusetts truly come alive during the autumn months. From fall foliage and charming inns to captivating art museums and exquisite farm-to-table dining, there are countless reasons to visit. Last week, I had the pleasure of exploring the Berkshires and experiencing its tight-knit community and natural serenity firsthand. During this adventure, I was captivated and inspired by the Berkshires’ eclectic character. I learned about its culture, history, and landscape, all while having the opportunity to relax and unwind. Here are 5 compelling reasons why you should visit the Berkshires this fall! Read more about the Berkshires. […]


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